Supporting Information
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- Charleen Bond
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1 Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry Yang,* a Emmanuel A. Theodorakis *a a Department of Chemistry & Biochemistry, University of California, San Diego, 9500 Gilman Drive MC: 0358, La Jolla, CA , USA. b Department of Pathology, University of California, San Diego, 9500 Gilman Drive MC: 0612, La Jolla, , USA * address: jerryyang@ucsd.edu * address: etheodor@ucsd.edu Supporting Information pages Experimental procedures 2-9 Fluorescent Spectra Kd determination MR spectra
2 General otes All reagents were purchased at highest commercial quality and used without further purification except where noted. Air- and moisture-sensitive liquids and solutions were transferred via syringe or stainless steel cannula. rganic solutions were concentrated by rotary evaporation below 45 C at approximately 20 mmhg. All non-aqueous reactions were carried out under anhydrous conditions. Yields refer to chromatographically and spectroscopically ( 1 H MR, 13 C MR) homogeneous materials, unless otherwise stated. Reactions were monitored by thin-layer chromatography (TLC) carried out on 0.25 mm Dynamic Adsorbents, Inc. silica gel plates (60F-254) and visualized under UV light and/or developed by dipping in solutions of 10% ethanolic phosphomolybdic acid (PMA) and applying heat. Dynamic Adsorbents, Inc. silica gel (60, particle size mm) was used for flash chromatography. MR spectra were recorded on the Varian Mercury 400, 300 and/or Unity 500 MHz instruments and calibrated using the residual non-deuterated solvent as an internal reference. The following abbreviations were used to explain the multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, b = broad. High resolution mass spectra (HRMS) were recorded on a VG 7070 HS mass spectrometer under electron spray ionization (ESI) or electron impact (EI) conditions. 6-bromo-2-naphtaldehyde (8) Br 8 H To a solution of DIBAL-H (1.0 M in heptane, 34 ml, 34 mmol) at 0 C under argon, a solution of 7 (3.0 gr, 11 mmol) in anhydrous THF was added dropwise. The reaction mixture was allowed to warm up to room temperature and left stirring overnight. Upon completion, MeH was added, followed by a saturated sodium potassium tartrate solution and ethylacetate. After the two phases were separated, the organic phase was washed with saturated solution of ammonium chloride and brine, dried over MgS 4 and concentrated under reduced pressure to yield 6-bromo-2-(hydroxymethyl)naphthalene. R f = 0.33 (EtAc:Hexanes 3:7); 1 H MR (400 MHz, CDCl 3 ): δ 7.99 (bs, 1H), 7.77 (bs, 1H), 7.74 (d, J= 8.5 Hz, 1H), 7.69 (d, J= 8.7 Hz, 1H), 7.55 (dd, J= 2
3 1.7, 8.7 Hz, 1H), 7.49 (dd, J= 1.7, 8.5 Hz, 1H), 4.84 (bs, 2H); 13 C MR (100 MHz, CDCl 3 ) δ 138.8, 133.9, 131.7, 129.7, 129.5, 129.5, 127.4, 126.1, 125.2, 119.8, To a suspension of pyridinium chlorochromate (2.4 gr, 11 mmol) in anhydrous CH 2 Cl 2 (60 ml) was added a solution of the above alcohol in anh. CH 2 Cl 2, and the reaction was heated under reflux for 5 hours. Upon completion, it was cooled to room temperature and poured into diethyl ether. The solution was then filtered through a pad of silica and concentrated under reduced pressure to yield 8 (2.4 gr, 95%). 8: white solid; R f = 0.67 (EtAc:Hexanes 3:7); 1 H MR (400 MHz, CDCl 3 ) δ (s, 1H), 8.31 (bs, 1H), 8.08 (bs, 1H), 7.98 (dd, J= 1.5, 8.5 Hz, 1H), 7.86 (m, 2H), 7.67 (dd, J= 1.5, 8.5 Hz, 1H); 13 C MR (100 MHz, CDCl 3 ) δ 191.8, 137.3, 134.3, 134.1, 131.0, 131.0, 130.6, 130.2, 128.2, 124.0, General procedure for the synthesis of 6-amino-substituted naphtaldehydes (9-12) In dry and degassed toluene (0.8 ml), were added Pd(Ac) 2 (0.022 mmol) and P(tBu) 3 (0.078 mmol) After stirring for 20 min, 8 (0.207 mmol), the appropriate amine (0.249 mmol) and Cs 2 C 3 (0.280 mmol) were added and the reaction left stirring for three days under reflux. After three days, the reaction was cooled at room temperature, diluted with CH 2 Cl 2, filtered, concentrated under reduced pressure and purified via silica gel flash chromatography (hexanes/etac 0-10%). 6-(piperidin-1-yl)naphthalene-2-carbaldehyde (9). 70% yield, yellow solid; R f = 9 H 0.61 (EtAc:Hexanes 3:7); 1 H MR (400 MHz, CDCl 3 ) δ (s, 1H), 8.15 (s, 1H), 7.83 (m, 2H), 7.68 (d, J= 8.6 Hz, 1H) 7.32 (dd, J= 2.4, 9.1 Hz, 1H), 7.08 (d, J= 2.4 Hz, 1H), 3.38 (m, 4H), (m, 6H); 13 C MR (100 MHz, CDCl 3 ) δ 191.9, 151.9, 138.5, 134.4, 131.3, 130.4, 127.2, 126.3, 123.4, 119.5, 108.8, 49.6, 25.5, 24.3; HRMS Calc for C 16 H 18 (M+H) found
4 6-morpholinonaphthalene-2-carbaldehyde (10). 79% yield, yellow solid; R f = 10 H 0.56 (EtAc:Hexanes 3:7); 1 H MR (400 MHz, CDCl 3 ) δ (s, 1H), 8.20 (s, 1H), 7.88 (m, 2H), 7.73 (d, J= 8.4 Hz, 1H), 7.32 (m, 1H), 7.11 (d, J= 1.2 Hz, 1H), 3.92 (m, 4H), 3.36 (m, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 191.9, 151.3, 138.1, 134.2, 131.8, 130.6, 127.5, 127.0, 123.6, 118.7, 109.0, 66.7, 48.5; HRMS Calc for C 15 H 15 2 a (M+a) found (4-methylpiperazin-1-yl)naphthalene-2-carbaldehyde (11). 77% yield, 11 H yellow solid; R f = 0.36 (EtAc:Hexanes 3:7); 1 H MR (300 MHz, CDCl 3 ) δ (s, 1H), 8.13 (s, 1H), 7.80 (m, 2H), 7.66 (d, J= 8.6 Hz, 1H), 7.28 (dd, J= 2.1, 9.2 Hz, 1H), 7.06 (d, J= 2.1 Hz, 1H), 3.36 (m, 4H), 2.57 (m, 4H), 2.33 (s, 3H); 13 C MR (100 MHz, CDCl 3 ) δ 191.5, 151.0, 138.0, 134.0, 131.3, 130.2, 127.1, 126.4, 123.1, 118.7, 108.7, 54.5, 47.8, 45.7; HRMS Calc for C 16 H 19 2 (M+H) found (2-morpholinoethylamino)naphthalene-2-carbaldehyde (12). 33% H 12 H yield, yellow solid; R f = 0.60 (2% MeH in CH 2 Cl 2 ); 1 H MR (400 MHz, CDCl 3 ) δ (s, 1H), 8.14 (s, 1H), 7.83 (dd, J= 1.6, 8.6 Hz, 1H), 7.76 (d, J= 8.9 Hz, 1H), 7.64 (d, J= 8.6 Hz, 1H), 6.98 (dd, J= 2.3, 8.9 Hz, 1H), 6.79 (d, J= 2.3 Hz, 1H), 4.88 (bs, 1H), 3.75 (m, 4H), 3.31 (dd, J= 5.1, 11.1 Hz, 2H), 2.72 (m, 2H), 2.51 (bs, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 191.9, 148.8, 139.1, 134.6, 130.8, 130.7, 126.6, 126.0, 123.8, 118.7, 103.8, 66.9, 56.7, 53.3, 39.3; HRMS Calc for C 17 H (M+H) found
5 General procedure for the synthesis of 2-cyanoacetates (13) To a solution of 2-cyanoacetic acid (2.72 mmol), the appropriate alcohol (2.27 mmol) in CH 2 Cl 2 (2.5 ml) and DMAP (0.013 mmol) was added dropwise at 0 C. Finally, DCC (2.72 mmol) was added and the reaction mixture was stirred at 0 C for 6 hours. The reaction was diluted with CH 2 Cl 2 and the formed DCU was filtered off. The filtrate was dried over MgS 4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography to yield 2-cyanoacetate 7. C 13a 2 2-(2-(2-methoxyethoxy)ethoxy)ethyl-2-cyanoacetate (13a). 86% yield; colorless liquid; R f = 0.45 (100% ether); 1 H MR (400 MHz, CDCl 3 ) δ 4.29 (m, 2H), 3.67, (m, 2H), 3.59 (m, 6H), 3.50 (m, 2H), 3.49 (s, 2H), 3.32 (s, 3H); 13 C MR (100 MHz, CDCl 3 ) δ 163.0, 113.0, 71.7, 70.4, 70.3, 68.3, 65.5, 58.8, 24.5; HRMS: calcd. for C 10 H 17 5 : (M+H + ) , found C 13b 3 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethyl-2-cyanoacetate (13b). 68% yield; colorless liquid; R f = 0.40 (100% ether); 1 H MR (400 MHz, CDCl 3 ) δ 4.21 (bs, 2H), 3.61 (bs, 2H), 3.51 (m, 12H), 3.43 (m, 2H), 3.24 (bs, 3H) 13 C MR (100 MHz, CDCl 3 ) δ 163.0, 113.0, 71.4, 70.2, 70.1, 70.1, 70.0, 68.1, 65.3, 58.5, 24.2; HRMS: calcd. for C 12 H 22 6 : (M+H + ) , found C 13c (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyanoacetate (13c). 71% yield; colorless liquid; R f = 0.83 (100% EtAc); 1 H MR (400 MHz, CDCl 3 ) δ 4.35 (m, 1H), (m, 2H), 4.09 (m, 1H), 3.76 (dd, J= 5.8, 8.6 Hz, 1H), 3.52 (s, 2H), 1.43 (s, 3H), 1.36 (s, 3H); 13 C MR (100 MHz, CDCl 3 ) δ 162.8, 112.7, 110.1, 73.0, 66.8, 65.9, 26.6, 25.2, 24.6; HRMS Calc for C 9 H 13 4 (M+H) found
6 General procedure for the synthesis of fluorescent probes To a round bottom flask containing a solution of aldehyde (0.21 mmol) and the appropriate 2- cyanoacetate (0.23 mmol) in THF (0.8 ml), piperidine (0.02 mmol) was added and the mixture left stirring at 50 C. The reaction was monitored by TLC and was completed within 21 hours. The crude mixture was concentrated under reduced pressure and the product was purified via flash column chromatography (10-30% EtAc in hexanes). C 6 (E)-2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-cyano-3-(2- (piperidin-1-yl)napthalen-6-yl) acrylate (6). 90% yield; red liquid; R f = 0.44 (EtAc:Hexanes 1:1); 1 H MR (400 MHz, CDCl 3 ) δ 8.31 (s, 1H), 8.22 (bs, 1H), 8.10 (d, J= 8.8 Hz, 1H), 7.76 (d, J= 9.2 Hz, 1H), 7.65 (d, J= 8.8 Hz, 1H), 7.30 (dd, J= 2.1, 9.2 Hz, 1H), 7.05 (d, J= 2.1 Hz, 1H), 4.47 (m, 2H), 3.83 (m, 2H), (m, 6H), 3.56 (m, 2H), (m, 4H), 3.37 (s, 3H), 1.74 (m, 6H); 13 C MR (100 MHz, CDCl 3 ) δ 163.3, 155.4, 151.9, 137.7, 134.7, 130.6, 127.2, 126.4, 125.9, 125.6, 119.2, 116.4, 108.3, 71.8, 70.7, 70.5, 70.5, 68.7, 65.3, 58.9, 49.3, 25.4, 24.3; HRMS Calc for C 26 H a (M+a) found C 14 (E)-2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-cyano-3- (2-(4-methylpiperazin-1-yl) napthalen-6-yl)acrylate (14). 85% yield; red liquid; R f = 0.71 (2% MeH in CH 2 Cl 2 ); 1 H MR (400 MHz, CDCl 3 ) δ 8.31 (s, 1H), 8.23 (s, 1H), 8.10 (d, J= 8.6 Hz, 1H), 7.78 (d, J= 9.1 Hz, 1H), 7.67 (d, J= 8.6 Hz, 1H), 7.29 (d, J= 9.1 Hz, 1H), 7.06 (s, 1H), 4.46 (m, 2H), 3.83 (m, 2H), 3.73 (m, 2H), 3.67 (m, 4H), 3.55 (m, 2H) 3.42 (bs, 4H), 3.36 (s, 3H), 2.61 (bs, 4H), 2.37 (s, 3H); 13 C MR (100 MHz, CDCl 3 ) δ 163.2, 155.4, 151.4, 137.5, 134.5, 130.6, 127.4, 126.9, 126.1, 126.1, 119.0, 116.2, 108.7, 99.3, 71.9, 70.8, 70.6, 70.5, 68.8, 65.4, 59.0, 54.8, 48.0, 46.1; HRMS Calc for C 26 H
7 (M+H) found C 15 (E)-2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-cyano-3- (2-morpholinonapthalen-6-yl) acrylate (15). 83% yield; red liquid; R f = 0.76 (2% MeH in CH 2 Cl 2 ); 1 H MR (300 MHz, CDCl 3 ) δ 8.31 (s, 1H), 8.24 (s, 1H), 8.11 (dd, J= 1.9, 8.8 Hz, 1H), 7.80 (d, J= 9.1 Hz, 1H), 7.69 (d, J= 8.8 Hz, 1H), 7.28 (m, 1H), 7.06 (d, J= 1.9 Hz, 1H), 4.47 (m, 2H), 3.90 (m, 4H), 3.83 (m, 2H), 3.70 (m, 6H), 3.55 (m, 2H), 3.35 (m, 7H); 13 C MR (100 MHz, CDCl 3 ) δ 163.0, 155.2, 151.3, 137.2, 134.4, 130.6, 127.4, 127.0, 126.1, 126.0, 118.5, 116.1, 108.5, 99.4, 71.8, 70.7, 70.5, 70.4, 68.6, 66.5, 65.3, 58.9, 48.2; HRMS Calc for C 25 H a (M+a) found H C 16 (E)-2-(2-(2-methoxyethoxy) ethoxy) ethyl3-(2- (2-morpholino ethylamino) naphthalene-6-yl)- 2-cyanoacrylate (16). 87% yield; red liquid; R f = 0.53 (2% MeH in CH 2 Cl 2 ); 1 H MR (500 MHz, CDCl 3 ) δ 8.28 (s, 1H), 8.19 (d, J= 1.6 Hz, 1H), 8.08 (dd, J= 1.9, 8.8 Hz, 1H), 7.69 (d, J= 8.9 Hz, 1H), 7.60 (d, J= 8.8 Hz, 1H), 6.95 (dd, J= 2.3, 8.8 Hz, 1H), 6.74 (d, J= 2.2 Hz, 1H), 4.96 (bs, 1H), 4.46 (m, 2H), 3.83 (m, 2H), (m, 6H), (m, 4H), (m, 2H), 3.36 (s, 3H), 3.31 (s, 2H), 2.70 (m, 2H), 2.51 (s, 4H); 13 C MR (100 MHz, CDCl 3 ) δ 163.4, 155.5, 149.0, 138.3, 135.0, 130.9, 126.6, 126.3, 126.2, 124.9, 118.9, 116.5, 103.6, 98.2, 71.9, 70.8, 70.6, 70.5, 68.8, 66.9, 65.3, 59.0, 56.6, 53.2, 39.2; HRMS Calc for C 27 H (M+H) found
8 C 17 (E)-2-(2-(2-(2-methoxyethoxy) ethoxy)ethoxy)ethyl 2-cyano-3-(2-(piperidin-1- yl)napthalen-6-yl)acrylate (17). 89% yield; red liquid; R f = 0.67 (2% MeH in CH 2 Cl 2 ); 1 H MR (400 MHz, CDCl 3 ) δ 8.20 (s, 1H), 8.10 (s, 1H), 8.01 (d, J= 8.5 Hz, 1H), 7.66 (d, J= 9.0 Hz, 1H), 7.55 (d, J= 9.0 Hz, 1H), 7.20 (d, J= 8.5 Hz, 1H), 6.95 (s, 1H), 4.39 (bs, 2H), 3.75 (bs, 2H), (m, 10H), 3.45 (m, 2H), 3.31 (bs, 4H), 3.28 (s, 3H), (m, 6H); 13 C MR (100 MHz, CDCl 3 ) δ 163.2, 155.3, 151.8, 137.6, 134.6, 130.5, 127.1, 126.3, 125.8, 125.5, 119.1, 116.3, 108.2, 98.4, 71.7, 70.6, 70.4, 70.3, 68.6, 65.3, 58.8, 49.2, 25.3, 24.2; HRMS Calc for C 28 H a (M+a) found C (E)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-3-(2- (piperidin-1-yl)naphthalene-6-yl) acrylate (18). 83% yield; red liquid; R f = 0.25 (EtAc:Hexanes 4:6); 1 H MR (400 MHz, CDCl 3 ) δ 8.29 (s, 1H), 8.19 (s, 1H), 8.09 (dd, J= 1.9, 8.8 Hz, 1H), 7.74 (d, J= 9.3 Hz, 1H), 7.63 (d, J= 8.8 Hz, 1H), 7.28 (dd, J= 2.8, 9.3 Hz, 1H), 7.03 (d, J= 1.9 Hz, 1H), 4.43 (m, 1H), 4.36 (m, 2H), 4.14 (dd, J= 6.0, 8.5 Hz, 1H), 3.90 (dd, J= 6.0, 8.5 Hz, 1H), 3.40 (m, 4H), (m, 6H), 1.48 (s, 3H), 1.39 (s, 3H); 13 C MR (100 MHz, CDCl 3 ) δ 162.9, 155.4, 151.5, 137.6, 134.6, 130.5, 127.0, 126.2, 125.6, 125.3, 119.0, 116.1, 109.6, 108.2, 98.0, 73.1, 65.9, 65.6, 57.1, 49.1, 45.5, 29.4, 26.4, 25.2, 24.0; MS (M+H) C H H (E)-2,3-dihydroxypropyl2-cyano-3-(2-(piperidin-1-yl) naphthalene- 6-yl)acrylate (19). Compound 18 (50 mgr, 0.12 mmol) was dissolved in a mixture of THF/MeH (1:1) and DWEX-H + resin (15 mgr) was added and the heterogeneous mixture was stirred for 20 hours. The resin was removed by 8
9 filtration and triethylamine was added and the solvent was removed under reduced pressure. The residue was purified by flash chromatography to give compound : 38 mgr, 84% yield; red liquid; R f = 0.55 (EtAc:Hexanes 1:4); 1 H MR (400 MHz, CDCl 3 ) δ 8.30 (s, 1H), 8.19 (s, 1H), 8.08 (d, J= 8.8 Hz, 1H), 7.74 (d, J= 9.1 Hz, 1H), 7.63 (d, J= 9.1 Hz, 1H), 7.29 (m, 1H), 7.03 (s, 1H), (m, 2H), 4.09 (m, 1H), 3.81 (dd, J= 5.5, 11.3 Hz, 1H), 3.73 (dd, J= 5.5, 11.3 Hz, 1H), 3.41 (m, 4H), (m, 6H); 13 C MR (100 MHz, CDCl 3 ) δ 163.6, 156.0, 152.0, 137.9, 135.0, 130.7, 127.3, 126.3, 125.9, 125.5, 119.2, 116.6, 108.3, 97.8, 69.9, 67.0, 63.2, 49.3, 25.5, 24.3; HRMS Calc for C 22 H (M+H) found
10 Fluorescence studies with aggregated Aβ peptides Compound 6 Intensity x Wavelength (nm) Before After mixing with Aβ Compound 14 Intensity x Before After mixing with Aβ Wavelength (nm) 10
11 Compound 15 Intensity x Before After mixing with Aβ Wavelength (nm) Compound 16 Intensity x Wavelength (nm) Before After mixing with Aβ 11
12 Compound 17 Intensity x Wavelength (nm) Before After mixing with Aβ Compound Before After mixing with Aβ Intensity x 10 3 Wavelength (nm) 12
13 Determination of binding constant Compound y = Bmax x / (K d + x) R 2 = Bmax = ± K d = ± Intensity (E) Concentration (um) Compound y = Bmax x / (K d + x) R 2 = Bmax = ± K d = ± Intensity (E) Concentration (um) 13
14 Compound y = Bmax x / (K d + x) R 2 = Bmax = ± K d = ± Intensity (E) Concentration (um) Compound y = Bmax x / (K d + x) R 2 = Bmax = ± K d = ± Intensity (E) Concentration (um) 14
15 Compound y = Bmax x / (K d + x) R 2 = Bmax = ± K d = ± Intensity (E) Concentration (um) Compound y = Bmax x / (K d + x) R 2 = Bmax = ± K d = ± Intensity (E) Wavelength (um) 15
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